Preparation of Ethyl Arylpropiolates from Aryl Iodides by Palladium-Catalyzed Cross-Coupling Reaction

Palladium-Catalyzed Alkynylation

“…The same solvent, which has been shown to be superior to THF in many organozinc crosscoupling reactions, was not used for the alkynylzinc reaction. In the same study, an indirect route involving the Sonogashira alkynylation of HCtCC(OEt) 3 was also reported, 95 but it does not appear to be a superior alternative to the alkynylzinc reaction.…”

Cross‐Coupling Reactions to sp Carbon Atoms

“…Alkynyltins are the most reactive organotin reagents, which make them particularly useful for cross-coupling [128]. In many instances where the preparatively simpler Sonogashira reaction is not successful, alkynylmetal couplings such as the Stille reaction give better results, such as with alkynes substituted with electron-withdrawing groups [129]. Base-sensitive compounds, which may degrade under the conditions used in the Sonogashira coupling, are often safe with the Stille reaction's neutral conditions.…”

Palladium and Copper Catalyzed Sonogashira cross Coupling an Excellent Methodology for C-C Bond Formation over 17 Years: A Review

“…It was noted that thermally stable palladium catalysts were also used for Sonogashira reaction [59]. In the literature survey, (PPh) 3 ligand was used for coupling of aryl halides with propiol-aldehyde diethyl acetal [60]. Lemhadri and coworkers used the tetrapodal phosphine ligand, Tedicyp 113 as a palladium source with copper for Sonogashira cross coupling of para-substituted aryl bromides with propiol-aldehyde diethyl acetal (Scheme 27).…”